Stabilized acrylic acid esters of polyhydric alcohols and a process for their preparation

Abstract

Acrylic acid esters of polyhydric alcohols can be stabilized by the addition of allyl compounds.

We claim: 
     
       1. A composition comprising an acrylic acid ester of a polyhydric alcohol having at least two acrylate moieties and a stabilizing amount of an allyl compound of the formula ##STR4## wherein R 1  -R 4  are hydrogen or alkyl having 1 to 4 carbon atoms; 
     
     
       X is chlorine, bromine, hydroxy, ##STR5## wherein R 5  is an n-valent aliphatic, araliphatic, cycloaliphatic or aromatic hydrocarbon radical which may contain free hydroxy moieties or --O-- linking moieties and R 6  is an n-valent aliphatic, cycloaliphatic, araliphatic or aromatic radical and n is an integer of from 1 to 4. 
     
     
       2. The composition of claim 1 wherein R 1  is hydrogen or methyl and R 2  -R 4  is hydrogen. 
     
     
       3. The composition of claim 1 including a polymerization inhibitor. 
     
     
       4. The composition of claim 1 wherein X is hydroxyl. 
     
     
       5. A process for preparing a stabilized acrylic acid ester of a polyhydric alcohol which comprises esterifying at least two hydroxyl moieties of a polyhydric alcohol with acrylic acid in the presence of a stabilizing amount of an allyl compound of the formula ##STR6## wherein R 1  -R 4  are hydrogen or alkyl having 1 to 4 carbon atoms; X is chlorine, bromine, hydroxy, ##STR7## wherein R 5  is an n-valent aliphatic, araliphatic, cycloaliphatic or aromatic hydrocarbon radical which may contain free hydroxy moieties or --O-- linking moieties and R 6  is an n-valvent aliphatic, cycloaliphatic, araliphatic or aromatic radical and n is an integer of from 1 to 4. 
     
     
       6. The process of claim 5 wherein said esterification is carried out under azeotropic conditions in the presence of at least one aliphatic hydrocarbon having a boiling point between about 40° and 80° C. as the entraining agent for removing water of reaction. 
     
     
       7. The process of claim 5 wherein an acid ion exchange resin is used as esterification catalyst.